TWI367201B - Process for preparing low-by-product methylglycine-n,n-diacetic acid tri(alkali metal) salts - Google Patents
Process for preparing low-by-product methylglycine-n,n-diacetic acid tri(alkali metal) saltsInfo
- Publication number
- TWI367201B TWI367201B TW095114901A TW95114901A TWI367201B TW I367201 B TWI367201 B TW I367201B TW 095114901 A TW095114901 A TW 095114901A TW 95114901 A TW95114901 A TW 95114901A TW I367201 B TWI367201 B TW I367201B
- Authority
- TW
- Taiwan
- Prior art keywords
- temperature
- methylglycine
- solution
- product
- alkali metal
- Prior art date
Links
- 229910052783 alkali metal Inorganic materials 0.000 title abstract 2
- 150000001340 alkali metals Chemical class 0.000 title abstract 2
- 239000006227 byproduct Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/26—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing carboxyl groups by reaction with HCN, or a salt thereof, and amines, or from aminonitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a process for preparing low-by-product, light-color methylglycine-N,N-diacetic acid tri(alkali metal) salt by alkaline hydrolysis of methylglycinediacetonitrile (MGDN), comprising the steps in the sequence (a) to (f): (a) mixing of MGDN with aqueous alkali at a temperature of ≰30° C.; (b) allowing the aqueous alkaline MGDN suspension to react at a temperature in the range from 10 to 30° C. over a period of from 0.1 to 10 h to form a solution; (c) allowing the solution from step (b) to react at a temperature in the range from 30 to 40° C. over a period of from 0.1 to 10 h; (d) optionally allowing the solution from step (c) to react at a temperature in the range from 50 to 80° C. over a period of from 0.5 to 2 h; (e) optionally allowing the solution from step (c) or (d) to react at a temperature in the range from 110 to 200° C. over a period of from 5 to 60 min; (f) hydrolysis and removal of ammonia of the solution obtained in step (c), (d) or (e) by stripping at a temperature of from 90 to 105° C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005021055A DE102005021055A1 (en) | 2005-05-06 | 2005-05-06 | Process for the preparation of low-by-product methylglycine-N, N-diacetic acid trialkali metal salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200704629A TW200704629A (en) | 2007-02-01 |
| TWI367201B true TWI367201B (en) | 2012-07-01 |
Family
ID=36615708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW095114901A TWI367201B (en) | 2005-05-06 | 2006-04-26 | Process for preparing low-by-product methylglycine-n,n-diacetic acid tri(alkali metal) salts |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7671234B2 (en) |
| EP (1) | EP1881957B1 (en) |
| JP (1) | JP4603613B2 (en) |
| KR (1) | KR20080015094A (en) |
| CN (1) | CN101171226B (en) |
| AT (1) | ATE520649T1 (en) |
| AU (1) | AU2006245816B2 (en) |
| BR (1) | BRPI0611122B1 (en) |
| CA (1) | CA2607232A1 (en) |
| DE (1) | DE102005021055A1 (en) |
| DK (1) | DK1881957T3 (en) |
| ES (1) | ES2370515T3 (en) |
| IL (1) | IL186680A (en) |
| MX (1) | MX2007013702A (en) |
| MY (1) | MY146034A (en) |
| NO (1) | NO20075532L (en) |
| PL (1) | PL1881957T3 (en) |
| PT (1) | PT1881957E (en) |
| RU (1) | RU2399611C2 (en) |
| TW (1) | TWI367201B (en) |
| UA (1) | UA87389C2 (en) |
| WO (1) | WO2006120129A1 (en) |
| ZA (1) | ZA200710628B (en) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2488291T3 (en) | 2009-10-12 | 2015-05-29 | Basf Se | Method for producing a powder containing one or more complexing agent salts |
| WO2012041741A1 (en) | 2010-09-27 | 2012-04-05 | Basf Se | Process for producing granules comprising one or more complexing agent salts |
| US8754026B2 (en) | 2010-09-27 | 2014-06-17 | Basf Se | Process for producing granules comprising one or more complexing agent salts |
| JP5914632B2 (en) * | 2011-04-04 | 2016-05-11 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Method for producing an aqueous solution of methylglycine-N, N-diacetic acid trialkali metal salt |
| MX2013011858A (en) * | 2011-04-12 | 2013-11-01 | Basf Se | Method for producing amino-polycarboxylates from amino acids. |
| WO2014090942A1 (en) | 2012-12-14 | 2014-06-19 | Akzo Nobel Chemicals International B.V. | Crystalline particles of glutamic acid n,n-diacetic acid |
| CN104854079A (en) | 2012-12-14 | 2015-08-19 | 阿克佐诺贝尔化学国际公司 | Crystalline particles of salts of glutamic acid n,n-diacetic acid |
| EP2774913B1 (en) * | 2013-03-08 | 2015-09-09 | Basf Se | Process for working up an aqueous solution or slurry of a complexing agent |
| WO2015036324A1 (en) * | 2013-09-13 | 2015-03-19 | Basf Se | Mixtures of enantiomers, and process for making such mixtures |
| EP3080074B1 (en) | 2013-12-09 | 2018-11-14 | Basf Se | Method of producing an aminocarboxylic acid |
| US20160304445A1 (en) * | 2013-12-11 | 2016-10-20 | Basf Se | N,n-bis(2-aminoalkyl)-1,2-alkyl diamine derivatives |
| CN103980136B (en) * | 2014-05-29 | 2016-05-11 | 重庆紫光化工股份有限公司 | The discoloration method of the aminocarboxylate feed liquid being made through alkaline hydrolysis by organic nitrile compound |
| JP6847034B2 (en) | 2014-10-17 | 2021-03-24 | ビーエイエスエフ・ソシエタス・エウロパエアBasf Se | Solution of trialkali metal salt of aminocarboxylic acid, its production and usage |
| AU2015371069B2 (en) | 2014-12-23 | 2019-08-22 | Akzo Nobel Chemicals International B.V. | Crystals of alanine N-acetic acid precursors, process to prepare them and their use |
| RU2712767C2 (en) * | 2015-03-11 | 2020-01-31 | Басф Се | Mixture of chelating agents and method of producing said mixtures |
| BR112017019108A2 (en) * | 2015-03-12 | 2018-04-17 | Basf Se | A process for the preparation of a mixture, mixture, aqueous solution, and uses of a composition and aqueous solution. |
| MX2017014525A (en) * | 2015-05-13 | 2018-03-12 | Basf Se | Process for making mixtures of chelating agents. |
| EP3216781A1 (en) | 2016-03-09 | 2017-09-13 | Basf Se | Mixtures containing potassium salts of methyl glycine diacetic acid |
| US10676700B2 (en) | 2016-04-06 | 2020-06-09 | Basf Se | Mixtures of chelating agents, and process for making such mixtures |
| WO2018086984A1 (en) | 2016-11-10 | 2018-05-17 | Basf Corporation | Process for increasing the production of hydrocarbons from hydrocarbon bearing reservoirs |
| CN106905176B (en) * | 2017-02-13 | 2019-07-09 | 湘潭大学 | Continuous hydrolysis prepares the method and self-oscillation reactor of imido oxalic acid |
| US11485703B2 (en) * | 2017-06-28 | 2022-11-01 | Basf Se | Process for manufacturing a complexing agent |
| CN114634420B (en) * | 2020-12-16 | 2023-09-19 | 万华化学集团股份有限公司 | A method for continuously preparing methylglycine-N,N-diacetic acid trialkali metal salt |
| WO2023278688A1 (en) | 2021-06-30 | 2023-01-05 | Ascend Performance Materials Operations Llc | Process for preparing nitrile intermediates for nitrogen-containing chelators |
| CN118812379A (en) * | 2024-06-14 | 2024-10-22 | 万华化学集团股份有限公司 | A method for preparing methylglycine-N,N-diacetic acid tri-alkali metal salt |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4840338B1 (en) * | 1969-02-21 | 1973-11-30 | ||
| US4547589A (en) * | 1984-01-03 | 1985-10-15 | Monsanto Company | Hydrolysis of nitrilotriacetonitrile |
| SU1288183A1 (en) * | 1985-03-11 | 1987-02-07 | Институт химических наук АН КазССР | Method of producing isonicotinic acid |
| DE4319935A1 (en) * | 1993-06-16 | 1994-12-22 | Basf Ag | Use of glycine-N, N-diacetic acid derivatives as complexing agents for alkaline earth and heavy metal ions |
| DE4444349A1 (en) * | 1994-12-14 | 1996-06-20 | Basf Ag | Use of glycine-N, N-diacetic acid derivatives as biodegradable complexing agents for alkaline earth and heavy metal ions in dye baths and dye treatment baths in the textile industry |
| DE19518986A1 (en) * | 1995-05-29 | 1996-12-05 | Basf Ag | Process for the preparation of glycine-N, N-diacetic acid derivatives by reacting glycine derivatives or their precursors with formaldehyde and hydrogen cyanide or iminodiacetonitrile or imindodiacetic acid with corresponding aldehydes and hydrogen cyanide in an aqueous acidic medium |
-
2005
- 2005-05-06 DE DE102005021055A patent/DE102005021055A1/en not_active Withdrawn
-
2006
- 2006-02-05 UA UAA200713656A patent/UA87389C2/en unknown
- 2006-04-26 TW TW095114901A patent/TWI367201B/en not_active IP Right Cessation
- 2006-04-26 MY MYPI20061918A patent/MY146034A/en unknown
- 2006-05-02 MX MX2007013702A patent/MX2007013702A/en active IP Right Grant
- 2006-05-02 CA CA002607232A patent/CA2607232A1/en not_active Abandoned
- 2006-05-02 ES ES06743390T patent/ES2370515T3/en active Active
- 2006-05-02 AT AT06743390T patent/ATE520649T1/en active
- 2006-05-02 RU RU2007144868/04A patent/RU2399611C2/en active
- 2006-05-02 PT PT06743390T patent/PT1881957E/en unknown
- 2006-05-02 US US11/913,597 patent/US7671234B2/en active Active
- 2006-05-02 DK DK06743390.4T patent/DK1881957T3/en active
- 2006-05-02 KR KR1020077028330A patent/KR20080015094A/en not_active Ceased
- 2006-05-02 EP EP06743390A patent/EP1881957B1/en not_active Not-in-force
- 2006-05-02 BR BRPI0611122-0A patent/BRPI0611122B1/en not_active IP Right Cessation
- 2006-05-02 JP JP2008509433A patent/JP4603613B2/en not_active Expired - Fee Related
- 2006-05-02 AU AU2006245816A patent/AU2006245816B2/en not_active Ceased
- 2006-05-02 WO PCT/EP2006/061968 patent/WO2006120129A1/en not_active Ceased
- 2006-05-02 PL PL06743390T patent/PL1881957T3/en unknown
- 2006-05-02 CN CN2006800154573A patent/CN101171226B/en not_active Expired - Fee Related
-
2007
- 2007-10-16 IL IL186680A patent/IL186680A/en not_active IP Right Cessation
- 2007-11-02 NO NO20075532A patent/NO20075532L/en not_active Application Discontinuation
- 2007-12-05 ZA ZA200710628A patent/ZA200710628B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007013702A (en) | 2008-01-21 |
| BRPI0611122A2 (en) | 2010-11-09 |
| ES2370515T3 (en) | 2011-12-19 |
| US20080194873A1 (en) | 2008-08-14 |
| IL186680A0 (en) | 2008-02-09 |
| DK1881957T3 (en) | 2011-11-21 |
| PL1881957T3 (en) | 2011-12-30 |
| IL186680A (en) | 2011-12-29 |
| MY146034A (en) | 2012-06-15 |
| DE102005021055A1 (en) | 2006-11-09 |
| ATE520649T1 (en) | 2011-09-15 |
| CA2607232A1 (en) | 2006-11-16 |
| TW200704629A (en) | 2007-02-01 |
| CN101171226A (en) | 2008-04-30 |
| US7671234B2 (en) | 2010-03-02 |
| BRPI0611122B1 (en) | 2015-08-11 |
| EP1881957A1 (en) | 2008-01-30 |
| AU2006245816B2 (en) | 2011-04-14 |
| WO2006120129A1 (en) | 2006-11-16 |
| JP2008540375A (en) | 2008-11-20 |
| PT1881957E (en) | 2011-09-01 |
| CN101171226B (en) | 2011-06-08 |
| KR20080015094A (en) | 2008-02-18 |
| NO20075532L (en) | 2008-02-04 |
| EP1881957B1 (en) | 2011-08-17 |
| UA87389C2 (en) | 2009-07-10 |
| ZA200710628B (en) | 2009-08-26 |
| AU2006245816A1 (en) | 2006-11-16 |
| RU2007144868A (en) | 2009-06-20 |
| JP4603613B2 (en) | 2010-12-22 |
| RU2399611C2 (en) | 2010-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |